1. Field of the Invention
This invention relates to novel organosilicon compounds. More particularly, this invention relates to organosilicon compounds containing one or two silicon atoms, at least two silicon-bonded alkoxy groups and at least one group that is bonded to silicon through oxygen and contains ethylenic unsaturation at a terminal position.
2. Description of the Prior Art
Certain types of silanes and other organosilicon compounds containing ethylenically unsaturated radicals bonded to silicon by means of an oxygen atom have been disclosed in the prior art.
Reaction products of ethylenically unsaturated epoxide compounds with chlorosilanes or bis-trichlorosilylhydrocarbon compounds of the general formula Cl.sub.3 SiQSiCl.sub.3 where Q represents alkylene, alkenylene, arylene or alkarylene are disclosed in U.S. Pat. No. 3,369,006, which issued to Brown on Feb. 13, 1968. All of these products contain a silicon-bonded chlorinated alkenyloxy radical of the general formula YCHClCH.sub.2 OSi, where Y represents an ethylenically unsaturated organic radical containing carbon, hydrogen and, optionally, oxygen and halogen.
1-alkenyloxysilanes wherein an ethylenically unsaturated carbon atom is bonded to an oxygen atom that is in turn bonded to silicon are disclosed in U.S. Pat. No. 3,472,888, which issued to Bazouin et al on Oct. 14, 1969, and in British Pat. No. 1,058,866 which issued on Feb. 15, 1967. Bazouin describes vinyloxysilanes that are reaction products of a chlorosilane, represented by the formula R.sub.n SiCl.sub.(4-n), with the enol form of an aldehyde or ketone, the enol compound being represented by the general formula R'R"C.dbd.CR"'OH. The products of this reaction exhibit the general formula R.sub.n SiO(R"')C.dbd.CR'R".sub.4-n, where R represents a monovalent organic radical, and R', R" and R"' each represent a hydrogen atom or a monovalent organic radical that is free of reactive substituents. The compounds described in the British patent can be represented by the same general formula used for Bazouin's compounds, with the proviso that the radicals represented by R', R" and R"' optionally contain ethylenic unsaturation which is reactive with carbon monoxide. The compounds of the British patent are prepared by reacting a terminally unsaturated hydrocarbon with (1) a silane containing a silicon-bonded hydrogen atom and (2) carbon monoxide.
The preparation of allyloxytrimethoxysilane is described by D. F. Peppard in articles that begin on pages 70 and 73 of volume 68 of the Journal of the American Chemical Society. The articles were published in 1946. The silane was prepared by reacting allyl alcohol with trimethoxychlorosilane in the presence of pyridine.